Yarn conditioning process and compositions therefor



Patented Sept. 8, 1942 V I 2,294,95 I YARN CONDITIONING PROCESS AND COMPOSITIONS THEREFOR John R. Caldwell, Kingsport, Temn, assignor to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application December16, 1940,

l Serial N0. 370,349

v I '10 Claims. (01. 2524.9) This invention relates to the conditioning of textile yarns, particularly those composed of or containing organic derivatives of cellulose such as cellulose acetate, celulose propionate, cellulose acetate propionate, cellulose acetate butyrate and of oils, although it may alsobe used to advantage inrormulas of the' latter type. t It is desirable that textile lubricants which are applied as oils, be ,of the clear'or homogeneous the like to render them more amenable to textile operations, and more particularly tothe compou ding of a conditioning agent for such yarns.

In'order that textile fibers may. be processed satisfactorily, itis essentialthat they be protected,

by a suitable lubricant. The need for proper lubrication is especially imperative in the case of cellulose acetate-and other continuous filament yarns. As the yarn passes throughguides and over rolls in the various processing steps, the filaments are continually subjected to an abrading and flexing action. If the surface friction be-.

tween fiber and guide reaches a certain value, the pull or drag exerted upon an individual filament exceeds its tensile strength, and the filament. is broken. In the case of celluloseacetate fibers, alubricant is usually applied while the yarn is beingspun, so that surface friction may be reduced to a minimum as'soon as possible, and thus simplii'y further processing. i I

In general, a satisfactoryloil must show the following properties: reduce surface 'friction be-..

tween yarn and guide, prevent the accumulation of excessive static electrification, impart a satisfactory feel or hand to the yarn, scour off readily, show some degree of stability towards ageing or oxidation, and have no tendency to injure the surface of the yarn.

Obviously, the use for which the yarn is in tended will have considerable bearing upon'the properties desired in the lubricant, e. g., a filling lubricant must show a higher drag or pull than a warp lubricant, to prevent sloughing from the type. .That is, the various components that make j up the blended oil'should be miscible or com-1 patible to the extent of forming a solution or mixture that will not separate into two or more phases after standing; Usually this degree of v homogeneity "is indicated by the fact-that the oil is clear to the unaided eye, and shows'no visible turbidity or suspended'matter.

It is common practice to include in the formula I of a blended oil one'or more emulsifying'agents such as a soap or sulphonated' oil in order to facilitate subsequent scouring and removal of lubricant from the-yarn. "Materials of this nature usually have a limited solubility in mineraland vegetable oils, and itis necessary to employ a third substance which acts as a cosolvent or.

blending agentbetween the oil andsoap cry-other emulsifying agent.

vThis invention has as an object to provide a new and improved agent for the lubrication and of or containing organic, derivatives of cellulose,

dressing of yarns, particularly those composed such as cellulose acetate, cellulose .,propionate,

cellulose acetate propionate and cellulose acetate butyrate Another object istofprovide -a yarn conditioning agent capable of lubricating, softening and rendering such yarns more amenableto varioustextile operations. A stilliurther object I is to provide ameans-of blending textile lubricop, while a warp 011 must have a certain afiinity for water or aqueous solutions to expedite sizing.

Since the various properties enumerated above are so diverse in nature, and since it is necessary.

qoindependently vary their relative magnitures, no single substance can fulfill all the requireents, and it is'necessary to resort to a mixture 1 blend of a number of components, each of which contributes toward the ultimate character I and value of the oil. It is the purpose of this invention to disclose a method whereby the incorporation or blending of several components into a mixture with desirable properties maybe facilitated.

"Textile lubricants are applied in twogeneral forms: i. e., as oils or as emulsions, and this invention is of particular value in the preparation cants, emulsifying agents and otheringredients customarily employed in'yarn lubricating agents; .1- Another object is to provide an improved method for the'conditioning oi yarns composed of or containing organic derivatives of cellulose. A San, further object is to provide an improved type. of

yarnvwhich is especially amenableto textile 'operations such as knitting, weaving, and theiike.

Other'objects will app ar hereinafter.

These objects are accomplished by the follow I ing invention which is based upon the discovery that alcohol-ethers formed by condensing certain di-olefinic terpenes with 'polyhydric alcohols ,or" their derivatives possessfi'unique and valuable properties, not only as yarn lubricants in and of themselves, but also as blending agents. the first place, these compounds are characterized by a long hydrocarbon ch'ain which gives them value as lubricants. In the second place, theyare characterized by the presence of anydroxyl group which tends to; impart miscibility with polar compounds such as -soapsgandformula is;

. sdrbitol,

probably has the structure;

sulfonated oils. In other words, these compounds are bifunctional and combine theproperties of a lubricant and blending agent in one individual. Furthermore, they are chemically neutral and do not exert any deleterious action whatever on the yarn, nor do they induce corrosion of the metallic parts of the textile machinery with which they come in contact,

In the following examples and description 1 have set forth several ofthe preferred embodiampss I r the terpenes, it is probable that the addition ocments of my invention, but they are included Y merely for purposes of illustration limitation thereof.

andnot as a,

' The compounds which I have found to be of particular value for the aforesaid purposes are terpene ethers of pclyhydric alcohols. These polyhydric Ialoohol, glycoljpolyhydric alcoholether or glycol ether with one molecule of a ter pene that contains It represents a hydrocarbon; radicalderived from a terpene, and containing one double bond. X

represents a radical containing one or more free compounds claimed here'iare curs at position 1.

Condensation is suitably carried out between a the terpene and the polyhydrlc alcohol by heating the two components in the presence of toluene sulfonic acid.

The terpene ethers maybe. used alone or in combination with other lubricating agents. For I example, the condensation product formed by reacting dlethylene glycol with depentene may be applied to yarn in various stages of processing by means of wick,roll, spray, etc.,'to the extent-of I 0.2%-10% based on the weight of the yarn. Yarns lubricated in this way are characterized by relatively low friction and a smooth, soft hand.

The terpenehydroxy ethers have their widest applications as components of mixed oils or lubricants. Because of their molecular structure which embodies a relatively long hydrocarbon chainand ether group in combination with the polar group --CHOH, they are valuable blending agents or cosolventsf'The hydrocarbon chain two double bonds, The general hydroxyl groups, derived from a polyhydric al- I cohol, glycol; glycol-ether, or polyhydric alcoholether. For example, the radical x may have the .5

structures,

-crn-cncm,-cra-on, etc.

Polyhydric alcohols and glycols which may be used include ethylene glycol. propylene glycol, trimethylene glycol, glycerine, mannitol, and

Ethers ofpolyhydric alcohols suitable for conand ether'group impart the property of solubility in oils, w ile the hydroxyl group tends to give miscibility. with polar compounds such as soaps, sulfonated oilsfetc. Y

Thus, we find that certain highly sulfonaud olive and cas'tor' oils will form turbid solutions when mixed'with-niineral oil. If a terpene ether is used in accordance with my invention as a geneous solution results.

The terpenehydroxy, ethers are excellent solthird component" of the mixture, a clear, homon vents for soaps and other emulsifying agents.

Thus, for example, oleicand stearic acid amine I soaps when mixed with the ethers form clear,

' stable solutionswhich may be applied to nbers by' the'usual methods. Alternatively, the solution of soap'in theterpene ether may be mixed with oils, fats,' waxes,- etc-.,' to form lubricants-and dressings of diverse types. The terpene hydroxyethers notonly lend themselves readily't'o the formation of stable oils, but

. also are easily adaptable to emulsii'ication procden'sation with the dl-oleflnic terpenes include diethylene glycol, dipropylene glycol, triethylene glycoL'and diglycerol;

Asstated, the terpenes used-in the process-of the invention contain two double bonds within the molecular structure. Examples of such terpenes are: alpha 'terpinene, dipentene; terpinolene, alpha or beta phellandrene, limonene, sylvestrene, and pseudolimonene. Mixtures of two or more di-olefinio terpenes may beused.

' The exact chemical-constitution of the addition-product is not known, but from a determina-. tion of the iodine'and acetyl values it canbeconeluded that thepolyhydrlc alcohol adds on at one of the double bonds inthe'terpene to form an ether. For example, in the case of alpha terpinene andethylene glycol, the'addition product The ether mirage could "be ade a carbons 3.10:4. but from the known re l 75 9 u my by esses. For example, a solution of soap and/or sulfonated oil in the terpene hydroxyethers forms afinely dispersed, stable emulsion when mixed with water. The ether solution of soap maybe mixed with a mineral oil, vegetable, 'or animal oil,' and the whole emulsified-by suitable treatmentv with'water. 1 My inventionwill be 'more readily understood by reference to the following examples which nlustrate typical yam treating compositions pre- Example 1 y l Percent. Sulf'onatedolive'oil 20 Mineral oil 50 Alpha terpinene-ethylene glycol addition pared in'accordance therewith and typical applications of such compositionsto the lubrication andconditioning of cellulose derivative yarns.

compound This lubricant may be applied as an oil by means of wick, roll, spray, etc.. or it may be emulsified and applied by similar means.

" Example 2 The compound formed by adding one molecule of diethylene glycol to one molecule of dipentene' is dissolved in a hydrocarbon solvent such as xylene orapetroleum fraction boiling at usual means, to the extent of 2%-20% based on the weight of the yarn treated.

Example 3 Terpinolene is condensed with one molecule of propylene glycol. Eighty parts of the product are terpene.

rived from a polyhydric alcohol and'a di-olefinic 3. The process of conditioning textile yarns mixed with 16 parts oleic acid and 4 parts monoethanolamine. This combination lends itselfwell to application as oil or emulsion.

This composition is especially suitable for emulsi- I fication as it disperses readily in water'to form a stable emulsion.

Example 5 OP-ive oil 20 Alpha terpinene-diethylene glycol addition compound 40 Monoethanolamine salt of sulfonated lauryl alcohol .20 Sperm oil 20 This lubricant may be applied the form of an oil or emulsion.

Although I have found it convenient to illus-. trate my invention by reference to the treatment of yarns composed of or containing organic de- Example 4 Mineral nil 65 Alpha terpinene-ethylene glycol addition product Coconut fatty acids 1 0 Diethanolamine 3 Sulfonated olive oil 10 'pene. 1 p a 6. A textile yarn lubricating and dressing comcomposed of or containing an organic derivative of cellulose to render such yarns amenable to textile operations such as knitting, weaving, spinning and the like which comprises applying thereto a yarn lubricant containing as an emulsifying agent a terpene ether derived from a polyhydric alcohol and a di-olefinic terpene;

4. Thep'rocess of conditioning textile yarns composed of or containing an organic derivative of cellulose to render such yarns amenable to textile operations such as knitting, weaving, spinning and the like which comprises applying thereto a lubricating composition containing atextile lubricant, an emulsifying agent for the lubricant, and as a blending'agent, for the lubricant and the emulsifying-agent a terpene ether, derived from a polyhydric alcohol and a di-olefinic ter- H P a 5, The process of conditioning textile yarns composed of or containing an organic derivative of cellulose to render such yarns 'amenable to textile operations such as knitting, weaving, spin-- ning and the like which comprises applying thereto a lubricating composition containing a textile lubricant, a soap and a terpene ether' derived from a polyhydric alcohol and a di-olefinic terposition containing a terpene ether derived from rivatives of cellulose such as cellulose acetate,

cellulose propionate, cellulose acetate propionate, cellulose acetate butyrate and the like, the yarn treating compositions described herein are broad- 1y applicable to the treatment of various-other synthetic as well as natural yarns. By the terms yam as used herein I refer to continuous synthetic filaments, natural and artificial staple fibers, mixtures of fibers of both synthetic and composed of or containing an organic derivative 1,

of cellulose to render such yarns amenable to textile operations such as knitting, weaving, spinning and the like which comprises applying thereto a composition containing a terpene ether dea polyhydric alcohol and a di-olefinic terpene.

7. A textile yarn lubricating and dressing compositioncontaining a textile lubricant, an emulsiiying agent for the lubricant, and as a blending agent for thelubricant and the emulsifying agent,

a terpene ether derived from a polyhydricalcohol and a di-olefinic terpene.-

8. A textile yarn lubricating position containing a textile lubricant, a soap and a terpene ether derived from a polyhydric alcohol and a di-olefinic terpene,"

9. A textile yarn amenable to operations such as knitting, weaving, spinning and the like impregnated with a lubricating and dressing composition containing a terpene ether derived from a polyhydric alcohol and 'a di-olefinic terpene.

10."A textile yarn composed'of' or containing an organic derivative'of cellulose amenable to operations such as knitting, weaving, spinning and the like impregnated-with a lubricating-and dressing composition containing a terpene ether derived from a polyhydric alcohol and a di-olefinic terpene.

JOHN R. I

and dressing c0m- 

